Benzyl ester of acetyl salicylic acid



Patented Nov. 21, 1922.

ET YATES l iidd ii ALFRED S. BURDIOK AND ELIVIER B. VLIET, OF CHICAGO, ILLINOIS, ASSIGNORS TO THE ABBOTT LABORATORIES, OF CHICAGO, ILLINOIS, A CORPORATION OF ILLINOIS.

IBENZYL ESTER OF ACETYL SALIOYLIC ACID.

N Drawing.

. To all whom it may concern:

Be it known that we, ALFRED S. BURDIGK and ELMER B. VLIET, both citizens of the United States, residing at Chicago, in the county of Cook and State of Illinois, have invented certain new and useful Improvements in Benzyl Ester of Acetyl Salicylic Acid, of which the following is a specification.

The object of our invention is to provide an improved compound for internal medication, which shall have pronounced antispasinodic properties in addition to the wellknown medicinal qualities possessed by aspirin, i. e. acetylsalicylic acid.

Preparation-Benzyl salicylate (1 mol.) is mixed with acetic anhydride (1;, mol.) and anhydrous sodium acetate mol.) and heated in an oil bath at 140 C. for 2 hours.

Upon cooling, the solution solidifies. This is brought into solution by triturating with benzene and water. The benzene solution is dried and distilled. The fraction distilling between 170200 C. at 5 min. pressure is collected. Upon long standing in an ice bath this solidifies and pure benzyl acetylsalicylate is obtained from this by several Serial No. 437,608.

crystallizations from a mixture of petroleum ether and carbon tetrachloride.

P1 0perties.The benzyl ester of acetylsalicylic acid is a white solid melting at 25.526 (l, which upon melting gives a straw colored, rather viscous liquid which has an index of refraction of 92% 1.5540.

Analysis.

0.1347 gms. substance0.3505 gins. CO 0.06414: gins. H O.

O l-l U Theory :C7 1.08% l-l5.22% Found 70.96% 5.35%

Benzyl acetylsalicylate is very soluble in carbon tetrachloride, benzene, xylene, ethyl acetate and acetone but is only slightly soluhle in petroleum ether. 0

Clinical tests indicate that this compound is an efiicient anti-spasn1odic in addition to having well-known desirable medicinal properties of acetylsalicylic acid.

Vi e claim as our invention:

The benzyl ester of acetylsalicylic acid.

ALFRED S. BURDICK. ELMER B. VLIET. 

